4-oxo-1-phenylpentan-3-yl acetate | 1026082-30-3

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 4-oxo-1-phenylpentan-3-yl acetate
• 英文别名: 3-(Acetyloxy)-5-phenyl-2-pentanone；(4-oxo-1-phenylpentan-3-yl) acetate
• CAS: 1026082-30-3
• 化学式: C₁₃H₁₆O₃
• 分子量: 220.268
• InChiKey: ZNKAVXDAADIFFH-UHFFFAOYSA-N

物化性质

• 沸点：
  336.6±42.0 °C(Predicted)
• 密度：
  1.070±0.06 g/cm3(Temp: 20 °C; Press: 760 Torr)(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.2
• 重原子数：
  16
• 可旋转键数：
  6
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.38
• 拓扑面积：
  43.4
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  4-oxo-1-phenylpentan-3-yl acetate 在 水 作用下， 生成 (+/-)-3-Hydroxy-5-phenyl-2-pentanone
  参考文献：
  名称：

  Samarium(II) Iodide Promoted Intermolecular Ketone-Olefin Couplings Chelation-Controlled by .alpha.-Hydroxyl Groups

  摘要：

  The hydroxyl group directed intermolecular ketone-olefin coupling reactions induced by SmI2 between alpha-hydroxyl ketones and alpha,beta-unsaturated esters occurred with excellent stereochemical control about the newly formed asymmetric centers.

  DOI：

  10.1021/jo00102a010
• 作为产物：
  描述：

  (+/-)-1-(2-Phenylethyl)-3-propynyl acetate 在 水 作用下， 以 1,4-二氧六环 为溶剂， 反应 12.0h， 以90%的产率得到4-oxo-1-phenylpentan-3-yl acetate
  参考文献：
  名称：

  炔丙基乙酸酯向α-酰氧基甲基酮的异质金（I）催化区域选择性水合

  摘要：

  已经开发出了炔丙基乙酸酯的多相金（I）催化区域选择性水合，可在室温下在1 mol％二苯膦改性的MCM-41固定的金（I）络合物存在下，在1,4-二恶烷中平稳进行。2 P-MCM-41-AuSbF 6 ]作为催化剂，为合成具有高原子经济性，良好至优异收率和高官能团耐受性的各种α-酰氧基甲基酮提供了一种高效实用的方法。这种新的固定化金（I）催化剂可以通过简单的制备程序轻松地从市售试剂中获得，并通过过滤过程进行回收，并至少重复使用7次，而活性没有明显降低。

  DOI：

  10.1016/j.jorganchem.2020.121136

文献信息

• Samarium(II) Iodide Promoted Intermolecular Ketone-Olefin Couplings Chelation-Controlled by .alpha.-Hydroxyl Groups
  作者：Motoi Kawatsura、Fuyuhiko Matsuda、Haruhisa Shirahama

  DOI：10.1021/jo00102a010

  日期：1994.11

  The hydroxyl group directed intermolecular ketone-olefin coupling reactions induced by SmI2 between alpha-hydroxyl ketones and alpha,beta-unsaturated esters occurred with excellent stereochemical control about the newly formed asymmetric centers.
• Hydroxyl-Directed Intermolecular Ketone-Olefin Couplings Promoted by SmI2
  作者：Fuyuhiko Matsuda、Motoi Kawatsura、Ken-ichi Hosaka、Haruhisa Shirahama

  DOI：10.1002/(sici)1521-3765(19991105)5:11<3252::aid-chem3252>3.0.co;2-d

  日期：1999.11.5

  SmI2-promoted intermolecular ketone-olefin couplings are facilitated and stereocontrolled by hydroxyl groups incorporated within the starting materials. For example, the SmI2-induced ketone - olefin coupling reactions of alpha-hydroxy ketone 5 with ethyl acrylate, acrylonitrile, ethyl crotonate, and 2(5 H)-furanone proceeded with high stereocontrol to afford the syn-1,2-diol products 6-9 in good yields. Excellent diastereoselectivity was achieved in the reductive couplings of beta-hydroxy aldehyde 21 and erythro-beta-hydroxy ketone 24 with acrylonitrile using SmI2, to produce the anti-1,3-diols 22 and 25 in good yields. The sense of the stereo-selectivity was in full accord with a chelation-control model. In the proposed model, the stereochemistry of the reaction product is explained by assuming that a cyclic ketyl radical is generated during the initial single-electron reduction by SmI2. This radical species results from the chelation of the Sm-III cation, attached to the ketyl radical, with the hydroxyl group.
• A heterogeneous gold(I)-catalyzed regioselective hydration of propargyl acetates toward α-acyloxy methyl ketones
  作者：Yingying Du、Fang Yao、Rongli Zhang、Mingzhong Cai

  DOI：10.1016/j.jorganchem.2020.121136

  日期：2020.3

  heterogeneous gold(I)-catalyzed regioselective hydration of propargyl acetates has been developed that proceeds smoothly in 1,4-dioxane at room temperature in the presence of 1 mol% diphenylphosphine-modified MCM-41-anchored gold(I) complex [Ph2P-MCM-41-AuSbF6] as catalyst and provides an efficient and practical approach for the synthesis of a variety of α-acyloxy methyl ketones with high atom economy

  已经开发出了炔丙基乙酸酯的多相金（I）催化区域选择性水合，可在室温下在1 mol％二苯膦改性的MCM-41固定的金（I）络合物存在下，在1,4-二恶烷中平稳进行。2 P-MCM-41-AuSbF 6 ]作为催化剂，为合成具有高原子经济性，良好至优异收率和高官能团耐受性的各种α-酰氧基甲基酮提供了一种高效实用的方法。这种新的固定化金（I）催化剂可以通过简单的制备程序轻松地从市售试剂中获得，并通过过滤过程进行回收，并至少重复使用7次，而活性没有明显降低。